I have a two-(almost three)-year-old, and I recently rented the new Winnie the Pooh movie for us to watch together. I had let him watch a couple Veggie Tale feature-lenth movies before, but other than that, this was his first "real" movie. I wasn't sure what to expect, but I figured Winnie the Pooh had to be pretty harmless.
My son was so excited about his "movie." And he loved it! He watched all 63 minutes and then wanted to watch it again (but I allow him only about an hour, max, a day). There were parts that were a little over his head. Owl uses particularly big words, and there are plays on words. But since Pooh doesn't understand big words either and since some of them get explained in smaller words, I figured it didn't matter too much. I'm not sure how much a two-year-old gets anyway (but I bet it's simultaneously more and less than we'd think). There are also humorous moments meant for older kids or the adults watching with them.
The only thing I was worried about was the monster the Hundred Acre Wood inhabitants think kidnapped Christopher Robin. This monster is called the "Backson," a misunderstanding created by a note Christopher leaves, which says he'll be "back soon." Adults will obviously get the mistake, but I'm not sure what my two-year-old thought. He didn't seem afraid of the music or dark woods, but that's something to watch for if you let your little ones see this.
Altogether, I thought it was a very appropriate introduction for little kids to Winnie the Pooh. The fact that it's a book is emphasized creatively with actual words and letters being part of the narration and story. At one point, the characters use letters (fallen off the page) as a ladder. It's rather clever but also very simple, and that goes for the whole story, too. Three stars.